Borane;tetrahydrofuran → 6-Bromo-1-(2-chloroethyl)-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

A round bottom flask was charged with 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-chloroethanone (compound 1, 0.546 g, 1.892 mmol) and treated with borane-THF complex (1M in THF, 18.9 mL, 18.9 mmol, 10 equivalents) and the resulting mixture stirred overnight at room temperature. After cooling to 0° C., the reaction was quenched by dropwise addition of methanol (5 mL) and stirred for 10 minutes at 0° C. The mixture was concentrated under reduced pressure and purified directly on silica gel eluting with 10% ethyl acetate/90% hexanes to yield a viscous residue, 2 (0.519 g, 100%). 1H-NMR (CDCl3) δ 7.11 (dd, 1H, J=8.7, 2.4 Hz), 7.08-7.04 (m, 1H), 6.42 (d, 1H, J=8.7), 3.64-3.56 (m, 4H), 3.35 (t, 2H, J=5.6 Hz), 2.73 (t, 2H, J=6.3 Hz), 1.97-1.89 (m, 2H). MS (ESI+): 274/276 (MH+, 100).

Provenance & Evidence